CN101175568B - 用于制备甲基丙烯酸的催化剂及其制备方法 - Google Patents
用于制备甲基丙烯酸的催化剂及其制备方法 Download PDFInfo
- Publication number
- CN101175568B CN101175568B CN2006800093175A CN200680009317A CN101175568B CN 101175568 B CN101175568 B CN 101175568B CN 2006800093175 A CN2006800093175 A CN 2006800093175A CN 200680009317 A CN200680009317 A CN 200680009317A CN 101175568 B CN101175568 B CN 101175568B
- Authority
- CN
- China
- Prior art keywords
- catalyst
- antimony
- methacrylic acid
- preparation
- methacrolein
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 title claims abstract description 45
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims description 31
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 33
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 30
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002131 composite material Substances 0.000 claims abstract description 28
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 22
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 20
- 239000011733 molybdenum Substances 0.000 claims abstract description 20
- 230000003197 catalytic effect Effects 0.000 claims abstract description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 18
- 239000011574 phosphorus Substances 0.000 claims abstract description 18
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 16
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 10
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims description 44
- 239000011248 coating agent Substances 0.000 claims description 40
- 239000000853 adhesive Substances 0.000 claims description 21
- 230000001070 adhesive effect Effects 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 17
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 12
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000320 mechanical mixture Substances 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 238000005245 sintering Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002002 slurry Substances 0.000 abstract description 40
- 238000006243 chemical reaction Methods 0.000 abstract description 39
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000011964 heteropoly acid Substances 0.000 abstract description 3
- 150000001463 antimony compounds Chemical class 0.000 abstract 2
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 28
- 239000007789 gas Substances 0.000 description 27
- 235000016768 molybdenum Nutrition 0.000 description 21
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000010949 copper Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 239000000919 ceramic Substances 0.000 description 8
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000012779 reinforcing material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- -1 propylene oxide aldehyde Chemical class 0.000 description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000003868 ammonium compounds Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229960004643 cupric oxide Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011268 mixed slurry Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical compound [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000021197 fiber intake Nutrition 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J27/14—Phosphorus; Compounds thereof
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- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
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- B01J37/03—Precipitation; Co-precipitation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/51—Spheres
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0027—Powdering
- B01J37/0045—Drying a slurry, e.g. spray drying
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP094734/2005 | 2005-03-29 | ||
| JP2005094734A JP4756890B2 (ja) | 2005-03-29 | 2005-03-29 | メタクリル酸製造用触媒及びその製造方法 |
| PCT/JP2006/306318 WO2006104155A1 (ja) | 2005-03-29 | 2006-03-28 | メタクリル酸製造用触媒及びその製造方法 |
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| CN201010143947XA Division CN101829589B (zh) | 2005-03-29 | 2006-03-28 | 用于制备甲基丙烯酸的催化剂及其制备方法 |
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| CN101175568B true CN101175568B (zh) | 2011-05-25 |
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| CN2006800093175A Expired - Fee Related CN101175568B (zh) | 2005-03-29 | 2006-03-28 | 用于制备甲基丙烯酸的催化剂及其制备方法 |
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| EP (2) | EP1867387B1 (ko) |
| JP (1) | JP4756890B2 (ko) |
| KR (2) | KR101223590B1 (ko) |
| CN (2) | CN101829589B (ko) |
| BR (1) | BRPI0608759A2 (ko) |
| CA (1) | CA2603005A1 (ko) |
| MY (1) | MY143359A (ko) |
| TW (1) | TW200642757A (ko) |
| WO (1) | WO2006104155A1 (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006314923A (ja) * | 2005-05-12 | 2006-11-24 | Nippon Kayaku Co Ltd | メタクリル酸製造用触媒の製造方法 |
| US8178718B2 (en) * | 2007-02-05 | 2012-05-15 | Saudi Basic Industries Corporation | Catalyst for oxidation of saturated and unsaturated aldehydes to unsaturated carboxylic acid, method of making and method of using thereof |
| WO2010052909A1 (ja) * | 2008-11-06 | 2010-05-14 | 日本化薬株式会社 | メタクリル酸の製造方法及びメタクリル酸製造用触媒 |
| JP5261231B2 (ja) * | 2009-03-04 | 2013-08-14 | 三菱レイヨン株式会社 | 不飽和カルボン酸合成用触媒の製造方法 |
| JP5570142B2 (ja) * | 2009-05-26 | 2014-08-13 | 日本化薬株式会社 | メタクリル酸製造触媒の製造方法およびメタクリル酸の製造方法 |
| JP5387297B2 (ja) * | 2009-09-30 | 2014-01-15 | 住友化学株式会社 | 複合酸化物触媒の製造方法 |
| CN102639238A (zh) * | 2009-11-30 | 2012-08-15 | 日本化药株式会社 | 异丁烯酸制造催化剂的制造方法及异丁烯酸的制造方法 |
| JP2012110806A (ja) * | 2010-11-22 | 2012-06-14 | Nippon Kayaku Co Ltd | メタクリル酸製造触媒の製造方法およびメタクリル酸の製造方法 |
| KR20140099453A (ko) * | 2011-11-17 | 2014-08-12 | 닛뽄 가야쿠 가부시키가이샤 | 메타크릴산 제조용 촉매 및 그것을 이용한 메타크릴산의 제조 방법 |
| US20150105583A1 (en) * | 2012-05-18 | 2015-04-16 | Nippon Kayaku Kabushiki Kaisha | Catalyst For Methacrylic Acid Production, Process For Producing The Same, And Process For Producing Methacrylic Acid Using The Catalyst |
| EP3056482B1 (en) | 2013-10-10 | 2020-06-17 | Nippon Kayaku Kabushiki Kaisha | Method for producing a supported catalyst |
| CN106140239A (zh) * | 2015-04-23 | 2016-11-23 | 北京化工大学 | 一种用于油品脱硫的多酸基负载型催化剂及其制备方法 |
| WO2018217961A1 (en) | 2017-05-25 | 2018-11-29 | Rohm And Haas Company | Process for preparing methacrolein |
| CN115888779B (zh) * | 2022-10-31 | 2024-05-28 | 鞍山七彩化学股份有限公司 | 一种丁二酸制备丁二腈的催化剂及丁二腈的制备方法 |
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| US4225466A (en) * | 1973-12-29 | 1980-09-30 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Catalytic oxide composition for preparing methacrylic acid |
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| DE2626887B2 (de) * | 1976-06-16 | 1978-06-29 | Basf Ag, 6700 Ludwigshafen | Katalysator für die Oxadation von (Methacrolein zu (Meth)Acrylsäure |
| JPS57165040A (en) | 1981-04-03 | 1982-10-09 | Sumitomo Chem Co Ltd | Preparation of catalyst for preparing methacrylic acid |
| JP2574948B2 (ja) | 1990-02-08 | 1997-01-22 | 株式会社日本触媒 | メタクリル酸の製造方法 |
| JP3146486B2 (ja) | 1990-06-28 | 2001-03-19 | 住友化学工業株式会社 | メタクリル酸製造用触媒の製造方法 |
| US5198579A (en) * | 1990-11-14 | 1993-03-30 | Mitsui Toatsu Chemicals, Inc. | Catalyst for oxidizing methacrolein and method for preparing methacrylic acid |
| JP3186243B2 (ja) | 1992-09-14 | 2001-07-11 | 三菱レイヨン株式会社 | メタクリル酸製造用触媒の調製法 |
| US5716895A (en) * | 1993-04-01 | 1998-02-10 | Nippon Kayaku Kabushiki Kaisha | Process for regeneration of catalysts |
| JPH08157414A (ja) | 1994-12-01 | 1996-06-18 | Mitsui Toatsu Chem Inc | メタクリル酸製造用触媒及びメタクリル酸の製造方法 |
| JP3482476B2 (ja) * | 1995-07-12 | 2003-12-22 | 住友化学工業株式会社 | メタクリル酸製造用触媒の製造方法およびメタクリル酸の製造方法 |
| JPH0924277A (ja) | 1995-07-14 | 1997-01-28 | Sumitomo Chem Co Ltd | メタクリル酸製造用触媒及びメタクリル酸の製造方法 |
| JPH09290162A (ja) | 1996-04-26 | 1997-11-11 | Mitsubishi Chem Corp | 酸化触媒の製造方法及びメタクリル酸の製造方法 |
| JP3799660B2 (ja) * | 1996-05-16 | 2006-07-19 | 三菱化学株式会社 | 酸化触媒及びその製造方法並びにメタクリル酸の製造方法 |
| US6339037B1 (en) | 1999-04-27 | 2002-01-15 | Nippon Shokubai Co. Ltd | Catalysts for methacrylic acid production and process for producing methacrylic acid |
| DE19922156A1 (de) | 1999-05-12 | 2000-08-10 | Basf Ag | Multimetalloxidmassen, Verfahren zu ihrer Herstellung, sowie Vorrichtungen zur Durchführung des Verfahrens |
| EP1325780A4 (en) * | 2000-09-21 | 2006-05-03 | Nippon Kayaku Kk | CATALYST FOR METHACRYLIC ACID PRODUCTION, COATED CATALYST AND METHOD FOR THE PRODUCTION THEREOF |
| JP3797148B2 (ja) * | 2001-06-29 | 2006-07-12 | 住友化学株式会社 | メタクリル酸製造用触媒の製造方法およびメタクリル酸の製造方法 |
| JP4200744B2 (ja) * | 2002-10-15 | 2008-12-24 | 住友化学株式会社 | メタクリル酸製造用触媒の製造方法およびメタクリル酸の製造方法 |
| MY144325A (en) | 2003-02-20 | 2011-08-29 | Nippon Kayaku Kk | Catalyst for producing methacrylic acid and preparation method thereof |
| MXPA05012783A (es) | 2003-05-30 | 2006-02-22 | Nippon Kayaku Kk | Metodo de preparacion de catalizador para producir acido metacrilico. |
| JP2005021727A (ja) * | 2003-06-30 | 2005-01-27 | Sumitomo Chem Co Ltd | メタクリル酸製造用触媒の製造方法及びメタクリル酸の製造方法 |
| JP2005058909A (ja) | 2003-08-12 | 2005-03-10 | Mitsubishi Rayon Co Ltd | メタクリル酸合成用触媒の製造方法 |
| JP4352856B2 (ja) | 2003-10-31 | 2009-10-28 | 住友化学株式会社 | メタクリル酸製造用触媒の製造方法、これにより得られるメタクリル酸製造用触媒、及びメタクリル酸の製造方法。 |
| JP4745653B2 (ja) | 2003-12-05 | 2011-08-10 | 三菱レイヨン株式会社 | メタクリル酸の製造方法 |
| JP4093194B2 (ja) * | 2004-03-23 | 2008-06-04 | 住友化学株式会社 | メタクリル酸の製造方法 |
| JP2006314923A (ja) | 2005-05-12 | 2006-11-24 | Nippon Kayaku Co Ltd | メタクリル酸製造用触媒の製造方法 |
-
2005
- 2005-03-29 JP JP2005094734A patent/JP4756890B2/ja not_active Expired - Fee Related
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2006
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- 2006-03-28 KR KR1020127009218A patent/KR101223590B1/ko not_active IP Right Cessation
- 2006-03-28 WO PCT/JP2006/306318 patent/WO2006104155A1/ja active Application Filing
- 2006-03-28 EP EP06730266.1A patent/EP1867387B1/en not_active Expired - Fee Related
- 2006-03-28 CA CA002603005A patent/CA2603005A1/en not_active Abandoned
- 2006-03-28 EP EP10156028A patent/EP2204234A1/en not_active Withdrawn
- 2006-03-28 CN CN2006800093175A patent/CN101175568B/zh not_active Expired - Fee Related
- 2006-03-28 BR BRPI0608759-0A patent/BRPI0608759A2/pt not_active IP Right Cessation
- 2006-03-28 KR KR1020077021745A patent/KR101208433B1/ko not_active IP Right Cessation
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- 2006-03-29 MY MYPI20061376A patent/MY143359A/en unknown
- 2006-03-29 TW TW095110953A patent/TW200642757A/zh not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4225466A (en) * | 1973-12-29 | 1980-09-30 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Catalytic oxide composition for preparing methacrylic acid |
Non-Patent Citations (4)
| Title |
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| JP特开2003-10691A 2003.01.14 |
| JP特开2004-188231A 2004.07.08 |
| JP特开2005-21727A 2005.01.27 |
| JP特开平9-75740A 1997.03.25 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101223590B1 (ko) | 2013-01-17 |
| JP2006272151A (ja) | 2006-10-12 |
| JP4756890B2 (ja) | 2011-08-24 |
| CN101175568A (zh) | 2008-05-07 |
| BRPI0608759A2 (pt) | 2010-01-26 |
| CN101829589A (zh) | 2010-09-15 |
| CA2603005A1 (en) | 2006-10-05 |
| EP1867387A1 (en) | 2007-12-19 |
| WO2006104155A1 (ja) | 2006-10-05 |
| US8716523B2 (en) | 2014-05-06 |
| EP1867387A4 (en) | 2009-09-02 |
| KR20070114362A (ko) | 2007-12-03 |
| EP1867387B1 (en) | 2013-12-04 |
| TWI374056B (ko) | 2012-10-11 |
| KR101208433B1 (ko) | 2012-12-05 |
| MY143359A (en) | 2011-04-29 |
| US20090234158A1 (en) | 2009-09-17 |
| EP2204234A1 (en) | 2010-07-07 |
| KR20120043152A (ko) | 2012-05-03 |
| TW200642757A (en) | 2006-12-16 |
| CN101829589B (zh) | 2013-08-21 |
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